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Chiral bUilding Blocks with bRidged or Caged polyclic structures

Project description

Synthetic methods for bridged and caged polycyclic scaffolds

For over 15 years, medicinal chemistry has focused on sp3-rich rigid polycyclic scaffolds, yet the demand for more stereogenic centres remains unmet due to synthetic challenges. The ERC-funded CUBIC project aims to develop new methods for enantioselective cycloadditions and cascade reactions to address this gap. These techniques will enable the enantioselective synthesis of bridged and caged polycyclic scaffolds, key to next-generation drug design. A major goal is the first enantioselective synthesis of a polysubstituted cubane scaffold, an enduring challenge in asymmetric synthesis. The project will also enable the first enantioselective total syntheses of several complex polycyclic natural products, opening new pathways for medicinal chemistry innovation.

Objective

Drug candidates should have a higher proportion of Csp3 over Csp2 and Csp and a greater number of stereogenic centers. That is essentially the message of F. Lovering et al. in their seminal article Escape from Flatland published in 2009 which induced a paradigm change in drug design. The first recommendation (higher proportion of Csp3) has opened a new field of research over the last 15 years, in a quest aiming at the synthesis and functionalization of small rigid polycyclic (bridged or caged) molecular scaffolds, used as building blocks in medicinal chemistry and particularly as bioisosteres of aromatics. This quest has strongly influenced academic and industrial research in organic and medicinal chemistry. However, the second recommendation (more stereogenic centers) was largely unmet due to the lack of efficient methods for the enantioselective synthesis of such chiral rigid polyclic structures.
In this project, we will develop an array of synthetic methods involving diverse enantioselective cycloadditions reactions and cascade transformations to fill this essential gap in knowledge. Ultimately, we will apply these methods to the enantioselective synthesis of various bridged and caged polycyclic scaffolds, which could become the building blocks of the future in drug design. In particular, we propose to achieve the first enantioselective synthesis of a polysubstituted cubane scaffold, a long-standing challenge in asymmetric synthesis. We will also apply these synthetic approaches to the unprecedented enantioselective total synthesis of various polycyclic natural products. Knocking down the scientific barrier of enantioselective synthesis of bridged and caged rigid molecular scaffolds will have huge repercussions for the fields of organic chemistry and asymmetric synthesis, through the development of new synthetic methods and total syntheses, but also for medicinal chemistry and drug discovery, via the design of the next generation of building blocks.

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Programme(s)

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Topic(s)

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Funding Scheme

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HORIZON-ERC - HORIZON ERC Grants

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Call for proposal

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(opens in new window) ERC-2024-COG

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Host institution

CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE CNRS
Net EU contribution

Net EU financial contribution. The sum of money that the participant receives, deducted by the EU contribution to its linked third party. It considers the distribution of the EU financial contribution between direct beneficiaries of the project and other types of participants, like third-party participants.

€ 1 999 758,00
Total cost

The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.

€ 1 999 758,00

Beneficiaries (1)

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